Pittsfield Vacation Rentals

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Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Pittsfield

Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is ￥87,254
￥160,473 total
includes taxes & fees
Jul 8 - Jul 9
Hancock Village Inn at Jiminy Peak
Tranquil Retreat 6-BRs Total in the Berkshires
TV, books, offices

Tranquil Retreat 6-BRs Total in the Berkshires

The price is ￥81,418
￥228,501 total
includes taxes & fees
Jul 7 - Jul 8
Tranquil Retreat 6-BRs Total in the Berkshires
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is ￥22,498
￥56,461 total
includes taxes & fees
Jul 9 - Jul 10
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Deluxe Queen Room with 2 Queen Beds
Property grounds

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is ￥17,363
￥22,654 total
includes taxes & fees
Jun 29 - Jun 30
Deluxe Queen Room with 2 Queen Beds
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is ￥69,307
￥125,659 total
includes taxes & fees
Jul 1 - Jul 2
Spacious 5-bedroom house in charming Lee with WiFi
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is ￥29,547
￥64,948 total
includes taxes & fees
Jun 30 - Jul 1
North Getaway Cottage
New Home - Heart of Williamstown 183
Living area

New Home - Heart of Williamstown 183

10.0 out of 10, Exceptional, (1)
"Great place to stay. House is brand new with plenty of room. Has 3 bedrooms plus a finished room in basement which is equivalent of a 4th room. Hiking and restaurants are close to the property. Plenty of parking. Highly recommend. Absolutely no complaints."
The price is ￥114,827
￥183,418 total
includes taxes & fees
Jun 30 - Jul 1
New Home - Heart of Williamstown 183
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is ￥36,769
￥54,925 total
includes taxes & fees
Jun 25 - Jun 26
Home in Great Barrington
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is ￥47,421
￥81,491 total
includes taxes & fees
Jun 25 - Jun 26
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (69)
"We had a wonderful stay, thank you! "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is ￥23,492
￥69,741 total
includes taxes & fees
Jun 28 - Jun 29
Comfortable Berkshires retreat on mtn resort, SISO
Enchanting Cottage, Come Enjoy Nature!
Dining

Enchanting Cottage, Come Enjoy Nature!

10.0 out of 10, Exceptional, (1)
"If you want TV, this isnt for you, but if you want a quiet place to check away and relax it fits the bill wonderfully"
The price is ￥76,457
￥150,638 total
includes taxes & fees
Jul 5 - Jul 6
Enchanting Cottage, Come Enjoy Nature!
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is ￥29,802
￥68,528 total
includes taxes & fees
Jun 26 - Jun 27
NEW RENO Historic Creamery in Berkshires w/hot tub
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is ￥38,228
￥87,143 total
includes taxes & fees
Jul 6 - Jul 7
Perfect House In Hillsdale, Brings Friends & Fam
Majestic views Hot tub Firepit Games Sleeps 14
Outdoor dining

Majestic views Hot tub Firepit Games Sleeps 14

The price is ￥161,868
￥266,328 total
includes taxes & fees
Jul 18 - Jul 19
Majestic views Hot tub Firepit Games Sleeps 14
Wolf Hill Acres: A Charming & Modern Country Home
Interior

Wolf Hill Acres: A Charming & Modern Country Home

10.0 out of 10, Exceptional, (1)
"7 of us, 60 year old friends plus young adult had a fabulous time over 4 days including NY’s eve, cooking together, playing pool,ping pong, watching movies, taking walks from house, a little time in Great Barrington, Hudson and Kingston! Great beds! We’re eager to come back iin summer!!"
The price is ￥110,760
￥211,276 total
includes taxes & fees
Jul 13 - Jul 14
Wolf Hill Acres: A Charming & Modern Country Home
Glass Lake Cottage
Outdoor dining

Glass Lake Cottage

The price is ￥48,515
￥97,582 total
includes taxes & fees
Jul 7 - Jul 8
Glass Lake Cottage
The Lakeshore House
Property grounds

The Lakeshore House

The price is ￥70,766
￥111,726 total
includes taxes & fees
Jul 7 - Jul 8
The Lakeshore House
Treat yourself at the stunning June Farms Wellness Huts!
Property grounds

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"Most AMAZING!!!!Going back sooooon!!!"
The price is ￥38,608
￥55,002 total
includes taxes & fees
Jul 1 - Jul 2
Treat yourself at the stunning June Farms Wellness Huts!
June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
Property grounds

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

9.8 out of 10, Exceptional, (8)
"We loved our stay here - it was beautiful, well appointed, and relaxing!"
The price is ￥38,608
￥62,129 total
includes taxes & fees
Jul 10 - Jul 11
June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

What's the top vacation rental that Pittsfield has to offer?

Lake Front Home in Heart of the Berkshires Near Jiminy Peak: Visitors give good reviews to this Pittsfield vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Some other top choices in Pittsfield are Hancock Village Inn at Jiminy Peak and Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table.

How many vacation rentals are there in Pittsfield?

With 37 Expedia vacation rentals, you're sure to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Barrington Stage Company.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.